Hydrochloric Acid → HCID 66611762, compound

HRID 2204717Notes

Reaction equation

HRID 2204717 reaction equation
[Cl:1][C:2]1[C:3]([C:26]([N:28]2[CH2:32][CH2:31][C:30]([F:34])([F:33])[CH2:29]2)=[O:27])=[CH:4][C:5]([O:18][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[C:6]([CH:17]=1)[C:7]([O:9]CC1C=CC=CC=1)=[O:8].[Li+].[OH-].O.Cl>O1CCCC1>[Cl:1][C:2]1[C:3]([C:26]([N:28]2[CH2:32][CH2:31][C:30]([F:34])([F:33])[CH2:29]2)=[O:27])=[CH:4][C:5]([O:18][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[C:6]([CH:17]=1)[C:7]([OH:9])=[O:8]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 3939Lithium HydroxideHCID 66612145HCID 66612145, compound

Product 1

HCID 66611762HCID 66611762, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
45 °C

Procedure

Phenylmethyl 5-chloro-4-[(3,3-difluoro-1-pyrrolidinyl)carbonyl]-2-[(phenylmethyl)oxy]benzoate (may be prepared as described in Description 64; 444 mg, 0.92 mmol) was dissolved in tetrahydrofuran (4 ml) and LiOH (66.6 mg, 2.78 mmol) and water (1 ml) were added. The solution was heated at 45° C. for 90 minutes. 2M Hydrochloric acid (1.39 ml, 2.78 mmol) was added and the solvent was removed in vacuo. The solid was partitioned between 2M HCl (5 ml) and ethyl acetate (40 ml), and the organic layer separated, dried (MgSO4) and the solvent removed in vacuo to give the title compound as a brown solid. 374 mg.

Workup

  1. customthe solvent was removed in vacuo
  2. customThe solid was partitioned between 2M HCl (5 ml) and ethyl acetate (40 ml)
  3. customthe organic layer separated
  4. dry with materialdried (MgSO4)
  5. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-cec5d6b832744b2d95708759a9e78d71
Source dataset
uspto-grants-2016_06
Patent number
US09365551B2

Reaction notes

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